Hydrochloric Acid → Methyl 4-bromo-2-methylbenzoate

HRID 2102914Notes

Reaction equation

HRID 2102914 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl.[CH3:13]O>C(OCC)C>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Bromo-2-methylbenzoic acid (5.0 g, 23 mmol) was suspended in methanol (30 mL). To the mixture was added a solution of HCl in diethylether (1.0M, 30 mL). The mixture was refluxed for 24 hours and concentrated to dryness. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give the desired compound (5.5 g) as a brown oil.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated sodium bicarbonate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9f87b2f8ec33486e80d9065b36df102e
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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